AGGREGATIVE ACTIVATION IN HETEROCYCLIC CHEMISTRY .4. METALATION OF 2-METHOXYPYRIDINE - UNUSUAL BEHAVIOR OF THE NEW UNIMETAL SUPERBASE BULI-ME2N(CH2)(2)OLI (BULI-LIDMAE)

A series of potential unimetal superbases BuLi-ROLi has been studied i n order to increase the basicity/ nucleophilicity ratio ([B/N]R) of Bu Li, The best [B/N]R ratio is found with BuLi-LiDMAE, This complex base apparently metallates 2-methoxypyridine at the unexpected Cd position , It is shown that no actual metallated species are formed in the reac tion medium, the reaction occurring as the result of a common radical precursor stabilized by an aggregate cluster. Finally, as an applicati on, Ca substituted 2-methoxypyridines have been obtained in good to ex cellent yields.